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| Names | |
|---|---|
| Preferred IUPAC name 4-[(1E,3S)-3-Ethenyl-3,7-dimethylocta-1,6-dien-1-yl]phenol | |
| Other names (+)-Bakuchiol | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.211.101 |
| EC Number |
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PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C18H24O | |
| Molar mass | 256.38 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Bakuchiol is a meroterpenoid (a chemical compound having a partial terpenoid structure) in the class terpenophenol. [1]
Contents
It was first isolated in 1966 by Mehta et al. from Psoralea corylifolia seed and was called Bakuchiol based on the Sanskrit name of the plant, Bakuchi. [2] Bakuchiol is a meroterpene phenol abundant in [3] and mainly obtained from the seeds of the Psoralea corylifolia plant, [4] [5] [6] which is widely used in Indian Ayurveda [7] to treat a variety of diseases. [8] It has also been isolated from other plants, such as P. grandulosa, [9] [10] P. drupaceae, [11] Ulmus davidiana, [12] Otholobium pubescens, [13] Piper longum [14] and Aerva sangulnolenta Blum. [15]
Even though the first complete synthesis of Bakuchiol was described in 1973, [16] its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol A by Sytheon Ltd. [17]
It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with resveratrol. [18] One study in rats suggested that Bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss. [19]
Bakuchiol possesses antioxidant, [20] [21] anti-inflammatory (in mice), [22] [23] and in vitro antibacterial [24] properties. Bakuchiol isolated from P. corylifolia has shown activity against numerous Gram-positive and Gram-negative oral pathogens. It was able to inhibit the growth of Streptococcus mutans under a range of sucrose concentrations, pH values and in the presence of organic acids in a temperature-dependent manner and also inhibited the growth of cells adhered to a glass surface. [25]
Despite having no structural resemblance to retinol, [26] Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression. [27] [28] In 2018, a randomized, double-blind, 12-week clinical study with 44 volunteers demonstrated that Bakuchiol is comparable with retinol in its ability to improve photoaging (wrinkles, hyperpigmentation) but has a better skin tolerance. [29]
Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation. [30]